Life After CEO: A Sabbatical of Building, Simulating, and Mentoring

After stepping down as CEO of Stack Overflow, Joel Spolsky has entered what he calls a sabbatical—not retirement—and he's busier than ever. In this article, we explore his current roles and the three companies he now chairs: Stack Overflow, Glitch, and HASH. From mentoring new leadership to fostering creative communities, Spolsky demonstrates that leaving the corner office can be a launchpad for new adventures.

A New Chapter: From CEO to Sabbatical

For the past few months, Prashanth Chandrasekar has been settling in as the new CEO of Stack Overflow. While Spolsky still joins customer calls and holds a weekly meeting with him, he has freed up significant time. Watching Chandrasekar reorganize the company—for the better—has been an eye-opening experience. Spolsky finds it deeply satisfying to realize that the best possible outcome for him is if Chandrasekar proves him a less effective CEO by running the company even more successfully. Living in what is jokingly called Manhattan's premier NORC (Naturally Occurring Retirement Community), Spolsky emphasizes he is on a sabbatical, not retiring. In fact, he is incredibly busy, and this update aims to answer the countless questions about his current activities.

Chairman at Stack Overflow: Still Involved, but Different

Spolsky remains chairman of Stack Overflow, a role he describes as familiar to most readers. The company continues to thrive under new leadership, and his focus now is on guiding strategy rather than day-to-day operations. This transition allows him to spend more time on other passions.

Glitch: Empowering the Next Generation of Web Developers

The company formerly known as Fog Creek Software has been rebranded as Glitch, positioned as “the friendly community for building the web.” Led by CEO Anil Dash, Glitch has grown to host millions of apps and secured substantial funding to accelerate growth. Spolsky believes that every era requires a simplified programming environment for the majority of developers who don't need complex Git branches or multi-step deployment processes. They simply want to write code and see it run. Glitch caters to that audience, making web development accessible to everyone.

HASH: Open Source Simulation for Complex Problems

The third company, HASH, operates somewhat under the radar but recently published extensive information on its website. Spolsky provides a preview: HASH is building an open-source platform for simulations. It models problems where you understand the behavior of individual agents but can't easily predict the aggregate outcome. For example, consider a city planner simulating traffic to argue for a new bus line. You could assume each bus removes 50 cars, but that only works if 50 commuters choose the bus—and their choice depends on travel time and cost savings. HASH allows simulating every agent's behavior, like in the game Cities: Skylines, and then testing thousands of potential bus routes to identify which ones actually reduce traffic. This kind of agent-based modeling is computationally intensive but effective when traditional formulas fall short.

Conclusion: Busy, Fulfilling, and Far from Retirement

With a two-year-old dog named Cooper (who might be looking for a mascot gig for your web app), Spolsky's days are full. He chairs three impactful companies, mentors new leaders, and explores innovative technology. Far from a quiet retirement, this sabbatical is a period of productive exploration and contribution. Whether it's guiding Stack Overflow's evolution, democratizing web development with Glitch, or tackling complex simulations with HASH, Spolsky remains deeply engaged in the tech world.